EP0551650B1 - Kombinationen aus Herbiziden und pflanzenschützenden Stoffen - Google Patents

Kombinationen aus Herbiziden und pflanzenschützenden Stoffen Download PDF

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Publication number
EP0551650B1
EP0551650B1 EP92121984A EP92121984A EP0551650B1 EP 0551650 B1 EP0551650 B1 EP 0551650B1 EP 92121984 A EP92121984 A EP 92121984A EP 92121984 A EP92121984 A EP 92121984A EP 0551650 B1 EP0551650 B1 EP 0551650B1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
hydrogen
haloalkyl
phenyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP92121984A
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German (de)
English (en)
French (fr)
Other versions
EP0551650A3 (enrdf_load_stackoverflow
EP0551650A2 (de
Inventor
Oswald Dr. Ort
Lothar Dr. Willms
Hans-Joachim Dr. Zeiss
Stephan Dr. Müller
Herbert Dr. Stark
Rainer Dr. Schütze
Klaus Dr. Bauer
Hermann Dr. Bieringer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Hoechst Schering Agrevo GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoechst Schering Agrevo GmbH filed Critical Hoechst Schering Agrevo GmbH
Priority to EP99105886A priority Critical patent/EP0943240B1/de
Publication of EP0551650A2 publication Critical patent/EP0551650A2/de
Publication of EP0551650A3 publication Critical patent/EP0551650A3/xx
Application granted granted Critical
Publication of EP0551650B1 publication Critical patent/EP0551650B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/561,2-Diazoles; Hydrogenated 1,2-diazoles
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647Triazoles; Hydrogenated triazoles
    • A01N43/6531,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • the invention relates to the technical field of crop protection agents, in particular Active ingredient-antidote combinations that are excellent for use against Harmful plants in crops are suitable.
  • Some newer herbicidal agents have very good efficacies and Selectivities and can fight a wide range of different weeds and / or grasses in special crops such as soybean, corn, Rice or cereals can be used. However, other crops are made by these herbicides are damaged, so that use in such crops is not at all is possible or only in small amounts that are not the optimal ensure broad herbicidal activity.
  • the herbicides of formula A or their salts are inhibitors of chlorophyll or. of carotenoid biosynthesis in plants. Take part in the treatment of the plants such active substances show lightening and white chlorosis on the leaves, which gradually grasp the whole plant and cause it to die (see Weed Technology, 1990, vol. 4, pages 731-738; WSSA Abstracts, vol. 31, 1991, Meeting WSSA Feb. 4-7, Abstr. 33, page 11; DE-A-4107141).
  • herbicides of formula A or their salts cannot selectively or at least not selectively in sufficiently high doses Grain crops and / or used in corn because these crops at least in the desired dosages for a broad herbicide Efficacy against weeds and grass weeds are required to be damaged.
  • herbicidal antidotes such as B. chloro- or bromoacetic acid amides, dichloroacetic acid amides, Thiazolidines, N-phenyl carbamates, N-phenylsulfonyl carbamates and 1,8-naphthalenedicarboxylic acid anhydride known (see EP-A-298679 and EP-A-298680).
  • safeners such as B. chloro- or bromoacetic acid amides, dichloroacetic acid amides, Thiazolidines, N-phenyl carbamates, N-phenylsulfonyl carbamates and 1,8-naphthalenedicarboxylic acid anhydride.
  • the crop e.g. B. wheat, before the damaging Effect of the herbicides are protected (cf. EP-A-298680, Tab. X, p 48).
  • alkyl, alkenyl and alkynyl are straight-chain or branched; the same applies to substituted alkyl, alkenyl and alkynyl radicals such as haloalkyl, hydroxyalkyl, alkoxycarbonyl, etc .; Alkyl means e.g. B.
  • Alkenyl means e.g. B. Allyl, 1-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methyl-but-3-ene and 1-methyl- but-2-ene; Alkynyl means e.g. B.
  • Halogen means fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, especially fluorine or chlorine;
  • Haloalkyl, alkenyl and alkynyl are alkyl, alkenyl and alkynyl, for example, substituted by halogen.
  • B. CF 3 , CHF 2 , CH 2 F, CF 3 CF 2 , CH 2 FCHCl, CCl 3 , CHCl 2 , CH 2 CH 2 Cl; Haloalkoxy is e.g. B.
  • phenyl is phenyl or substituted phenyl; substituted phenyl is phenyl which is monosubstituted or polysubstituted by radicals from the group halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 -haloalkoxy and nitro is substituted, e.g. B.
  • the compounds of formula B1 are from EP-A-0333131 (ZA-89/1960), EP-A-0269806 (US-A-4,891,057), EP-A-0346620 (AU-A-89/34951), WO-91/08202 (International patent application PCT / EP 90/01966) and WO-91/07874 (International Patent Application No. PCT / EP 90/02020) and literature cited therein known or can by or analogous to the methods described therein getting produced.
  • the compounds of the formula B2 are from EP-A-94349 (US-A4,902,340), EP-A-0191736 (US-A-4,881,966) and the German patent application P 4041121.4 (EP-A-0492366, ZA-91/9981) and the literature cited therein are known or can be produced by or analogously to the processes described there.
  • 2-acylated cyclic 1,3-dicarbonyl compounds are suitable as compounds A. or their salts, which are only in combination with Type B compounds favorably in cereal crops, rice and / or corn can be used because they alone without the type B safener Damage crops too much.
  • Tables 1 to 5 below give examples of the abovementioned herbicidal 2-acyl-1,3-dicarbonyl compounds of the formula A.
  • the meanings of the radicals each relate to the formula given at the top of the table.
  • imidazolinones are suitable for use with the safeners B. become; the sulfonylureas and imidazolinones are, for example, in EP-A-0492366 (ZA-91/9981).
  • the herbicidal active ingredients and the safeners mentioned can be taken together (as finished Formulation or in the tank mix method) or in any order one after the other be applied.
  • the weight ratio safener: herbicide can continue within Limits vary and is preferably in the range of 1:10 to 10: 1, in particular from 1:10 to 5: 1.
  • the optimal amounts of herbicide and safener are of the type of the herbicide used or of the safener used and of the type of treating crops depend on and from case to case determine appropriate preliminary tests.
  • the main areas of application for the application of safeners are mainly cereal crops (Wheat, rye, barley, oats), rice, corn, sorghum, but also cotton and Soybean, preferably cereals and corn.
  • Type 3 safeners can be used for pretreatment of the seed of the crop (dressing the seeds) are used or before the seed is introduced into the seed furrows or together with the herbicide before or be applied after emergence of the plants.
  • Pre-emergence treatment includes both the treatment of the acreage before sowing and the Treatment of the sown but not overgrown areas.
  • Co-application with the herbicide is preferred in Post-emergence procedure. For this purpose tank mixes or ready formulations be used.
  • the required application rates of the safener can vary depending on the indication and Herbicide used fluctuate within wide limits and are usually in the Range of 0.001 to 5 kg, preferably 0.005 to 0.5 kg of active ingredient per hectare.
  • the present invention therefore also relates to a method for protection of crops before phytotoxic side effects of herbicidal compounds A, which is characterized in that an effective amount of a compound of Formula B1 mentioned before, after or simultaneously with herbicide A, preferably together with the herbicide A in the post-emergence process Plants, plant seeds or the cultivated area is applied.
  • the compounds B and their combinations with one or more of the Herbicides mentioned can be formulated in different ways, depending on which biological and / or chemical-physical parameters are specified.
  • Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable Solutions, suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, Granules for spreading and soil application, granules (GR) in the form of micro, Spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powder
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • EW emulsions
  • SC suspension concentrates
  • SC dispersions based on oil or water, oil-miscible solutions
  • the necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are, for example described in: Watkins, “Handbook of Insecticide Dust Diluent and Carriers", 2nd Ed., Darland Books; Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, N.Y .; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ.
  • pesticidal substances e.g. Insecticides, acaricides, herbicides, fungicides, Manufacture safeners, fertilizers and / or growth regulators, e.g. in form of a Ready formulation or as a tank mix.
  • Spray powders are preparations which are uniformly dispersible in water Active ingredient and / or safener in addition to a diluent or inert substance or surfactants ionic and / or nonionic type (wetting agent, dispersing agent), e.g.
  • polyoxyethylated alkylphenols polyoxethylated fatty alcohols, polyoxethylated fatty amines, Fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonic acid, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene-sulfonic acid sodium or oleoylmethyltauric acid sodium contain.
  • the herbicidal active ingredients are used to produce the wettable powders for example in conventional equipment such as hammer mills, fan mills and Air jet mills finely ground and simultaneously or subsequently with the Formulation aids mixed.
  • Emulsifiable concentrates are obtained by dissolving the active ingredient or active ingredient and / or safener in an organic solvent, e.g. butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more ionic and / or nonionic surfactants ( Emulsifiers).
  • an organic solvent e.g. butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more ionic and / or nonionic surfactants ( Emulsifiers).
  • alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or nonionic emulsifiers
  • fatty acid polyglycol esters alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as e.g. B. sorbitan fatty acid esters or polyoxethylene sorbitan esters such.
  • B. polyoxyethylene sorbitan fatty acid ester examples of emulsifiers which can be used are: alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan
  • Dusts are obtained by grinding the active ingredient and / or safener with fine distributed solid materials, e.g. Talc, natural clays such as kaolin, bentonite and Pyrophyllite, or diatomaceous earth.
  • fine distributed solid materials e.g. Talc, natural clays such as kaolin, bentonite and Pyrophyllite, or diatomaceous earth.
  • Suspension concentrates can be water or oil based. You can for example by wet grinding using commercially available pearl mills and optionally addition of surfactants, such as. B. above with the others Formulation types already listed can be produced.
  • Emulsions e.g. B. oil-in-water emulsions (EW) can be used, for example Stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, such as z. B. above in the other types of formulation are already listed.
  • EW oil-in-water emulsions
  • Granules can either by spraying the active ingredient and / or safener adsorbable, granulated inert material can be produced or by application of active ingredient concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid Sodium or mineral oils on the surface of carriers such as sand, Kaolinite or granulated inert material.
  • adhesives e.g. Polyvinyl alcohol, polyacrylic acid Sodium or mineral oils on the surface of carriers such as sand, Kaolinite or granulated inert material.
  • Suitable active ingredients in the usual for the production of fertilizer granules - if desired in Mix with fertilizers - be granulated.
  • Water-dispersible granules are usually produced using the usual methods Spray drying, fluid bed granulation, plate granulation, mixing with High speed mixers and extrusion made without solid inert material.
  • Spray drying for the production of plate, fluidized bed, extruder and spray granules, see e.g. Procedure in "Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration”, Chemical and Engineering 1967, pages 147 ff; "Perry's Chemical Engineer's Handbook ", 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.
  • the agrochemical preparations usually contain 0.1 to 99 % By weight, in particular 0.1 to 95% by weight, of active compound of the formula (I).
  • the active substance concentration in wettable powders is e.g. about 10 to 90% by weight, of the The remainder to 100 wt .-% consists of conventional formulation components.
  • the active ingredient concentration can be about 1 to 90, preferably 5 to 80 wt .-%.
  • Dusty formulations contain 1 to 30, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions, for example 0.05 to 80, preferably 2 to 50 wt .-% active ingredient.
  • the active ingredient content depends in part on whether the active compound is liquid or solid and which granulation aids, fillers etc. are used become.
  • the active ingredient content is in the water-dispersible granules for example between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active ingredient formulations mentioned may each contain usual adhesive, wetting, dispersing, emulsifying, penetration, preservation, Antifreeze and solvents, fillers, carriers and dyes, defoamers, Evaporation inhibitors and agents that affect pH and viscosity.
  • the formulations available in commercial form are used optionally diluted in a conventional manner, e.g. with wettable powders, emulsifiable Concentrates, dispersions and water-dispersible granules using water. Dust-like preparations, granules and sprayable solutions are used before Application usually no longer diluted with other inert substances.
  • Especially good efficacies of the agents according to the invention can be achieved if in addition to the surfactants contained in the formulations Concentrations of 0.1 to 0.5 wt .-% are added in the tank mix process, for.
  • the crops, weeds and weeds were grown outdoors or in the greenhouse grown in plastic pots up to the 4- to 5-leaf stage and then according to the invention with compounds of type A) and B) in the post-emergence process treated.
  • the compounds of types A) and B) became more aqueous in the form Suspensions or emulsions with a water application rate of the equivalent of 300 I / ha applied. 4 weeks after treatment, the plants were visually examined on each Type of damage from the herbicides applied, in particular the extent of persistent plant damage was taken into account. The review was done in percentages compared to untreated controls.
  • Tables 6 and 7 illustrate that the type B compounds used according to the invention can effectively reduce severe herbicide damage to crop plants. Even if the herbicides are overdosed, severe damage to crops is significantly reduced and less damage is completely eliminated. Mixtures of herbicides and compounds of type B are therefore excellent for selective weed control in crops such as cereals and maize.

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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP92121984A 1991-12-31 1992-12-24 Kombinationen aus Herbiziden und pflanzenschützenden Stoffen Expired - Lifetime EP0551650B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP99105886A EP0943240B1 (de) 1991-12-31 1992-12-24 Kombinationen aus Herbiziden und pflanzenschützenden Stoffen

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4143253 1991-12-31
DE4143253 1991-12-31

Related Child Applications (1)

Application Number Title Priority Date Filing Date
EP99105886A Division EP0943240B1 (de) 1991-12-31 1992-12-24 Kombinationen aus Herbiziden und pflanzenschützenden Stoffen

Publications (3)

Publication Number Publication Date
EP0551650A2 EP0551650A2 (de) 1993-07-21
EP0551650A3 EP0551650A3 (enrdf_load_stackoverflow) 1994-02-02
EP0551650B1 true EP0551650B1 (de) 1999-10-13

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Family Applications (2)

Application Number Title Priority Date Filing Date
EP92121984A Expired - Lifetime EP0551650B1 (de) 1991-12-31 1992-12-24 Kombinationen aus Herbiziden und pflanzenschützenden Stoffen
EP99105886A Expired - Lifetime EP0943240B1 (de) 1991-12-31 1992-12-24 Kombinationen aus Herbiziden und pflanzenschützenden Stoffen

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EP99105886A Expired - Lifetime EP0943240B1 (de) 1991-12-31 1992-12-24 Kombinationen aus Herbiziden und pflanzenschützenden Stoffen

Country Status (6)

Country Link
US (1) US5441922A (enrdf_load_stackoverflow)
EP (2) EP0551650B1 (enrdf_load_stackoverflow)
JP (1) JP3413227B2 (enrdf_load_stackoverflow)
AU (1) AU662581B2 (enrdf_load_stackoverflow)
CA (1) CA2086491C (enrdf_load_stackoverflow)
DE (2) DE59209757D1 (enrdf_load_stackoverflow)

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KR927002913A (ko) * 1989-10-18 1992-12-17 짜우너, 라피체 제초 활성 물질 혼합물
DE3939010A1 (de) * 1989-11-25 1991-05-29 Hoechst Ag Isoxazoline, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschuetzende mittel
DE3939503A1 (de) * 1989-11-30 1991-06-06 Hoechst Ag Neue pyrazoline zum schutz von kulturpflanzen gegenueber herbiziden
CA2115567A1 (en) * 1991-08-22 1993-03-04 Brett Hayden Bussler Safening herbicidal pyrazolylsulfonylureas

Also Published As

Publication number Publication date
EP0551650A3 (enrdf_load_stackoverflow) 1994-02-02
EP0943240B1 (de) 2001-11-14
DE59209757D1 (de) 1999-11-18
AU662581B2 (en) 1995-09-07
DE59209933D1 (de) 2001-12-20
AU3047792A (en) 1993-07-08
CA2086491A1 (en) 1993-07-01
JPH05279204A (ja) 1993-10-26
EP0943240A3 (de) 1999-10-13
EP0943240A2 (de) 1999-09-22
US5441922A (en) 1995-08-15
JP3413227B2 (ja) 2003-06-03
CA2086491C (en) 2003-09-16
EP0551650A2 (de) 1993-07-21

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